This article draws on several crucial and unpublished manuscripts from the Scholem Archive in exploration of Gershom Scholem's youthful statements on mathematics and its relation to extra-mathematical facts and, more broadly, to a concept of history that would prove to be consequential for Walter Benjamin's own thinking on "messianism" and a "futuristic politics." In context of critiquing the German Youth Movement's subsumption of active life to the nationalistic conditions of the "earth" during the First World War, Scholem turns to mathematics for a genuine and self-consistent theory of action. In the concept of actual infinity (in Cantor and Bolzano) he finds an explanation of how mathematics relates to "the physical" without reducing the former to an "image" of the latter, and without relying on the concept of geometric intuition. This explanation, insofar as it relies on the notion of actual infinity, provides Scholem with a conception of mathematics (and the history of mathematics) that reconciles freedom and necessity—remarks on which he outlines in his diaries and communicates to Benjamin in early March 1916.